Epoxidation of stereoisomeric substituted norbornenes. Kinetic and theoretical investigation

Russian Journal of Organic Chemistry

Volumn 36, Issue 2, 2000, Pages 195-202

  Kas'yan, L I ^a   Okovityi, S I ^a   Bomushkar', M F ^a   Driuk, V G ^a  

^a OLES HONCHAR DNIPRO NATIONAL UNIVERSITY   (Ukraine)

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EID: 0034134997     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (65)

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12. 3. Freeman, F., Chem. Rev., 1975, vol. 75, no. 4, pp. 439-490; Kas'yan, L.I., Ctepanova, N.V., Bykov, M.V., and Malinovskii, M.C., Ukr. Khim. Zh., 1984, vol. 50, no. 6, pp. 633-637; Huisgen, R., Ooms, P.H.J., Mingin, M., and Allinger, N.L., J. Am. Chem. Soc., 1980, vol. 102, no. 11, pp. 3951-3953; Kas'yan, L.I., Gorb, L.G., Ctepanova, N.V., and Zefirov, N.C., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 893-897; Burkert, N., Angew. Chem., 1981, vol. 93, no. 6-7, pp. 602-603; Houk, K.N., Rondan, N.G. Brown, F.K., Jorgensen, W.L., Madura, J.D., and Spellmeyer, D.C., J. Am. Chem. Soc., 1983, vol. 105, no. 19, pp. 5980-5988; Spanget-Lansen, J., and Gleiter, R., Tetrahedron, 1983, vol. 39, no. 20, pp. 3345-3350; Carrupt, P.-A. and Vogel, P., J. Mol. Struct. (Theochem.), 1985, vol. 124, nos. 1-2, pp. 9-23; Rondan, N.G., Paddon, Row, M.N., and Carammella, P., Mareda, J., Mueller, P.H., and Houk, K.N., J. Am. Chem. Soc., 1982, vol. 104, no. 18, pp. 4974-4976.
13. 3. Freeman, F., Chem. Rev., 1975, vol. 75, no. 4, pp. 439-490; Kas'yan, L.I., Ctepanova, N.V., Bykov, M.V., and Malinovskii, M.C., Ukr. Khim. Zh., 1984, vol. 50, no. 6, pp. 633-637; Huisgen, R., Ooms, P.H.J., Mingin, M., and Allinger, N.L., J. Am. Chem. Soc., 1980, vol. 102, no. 11, pp. 3951-3953; Kas'yan, L.I., Gorb, L.G., Ctepanova, N.V., and Zefirov, N.C., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 893-897; Burkert, N., Angew. Chem., 1981, vol. 93, no. 6-7, pp. 602-603; Houk, K.N., Rondan, N.G. Brown, F.K., Jorgensen, W.L., Madura, J.D., and Spellmeyer, D.C., J. Am. Chem. Soc., 1983, vol. 105, no. 19, pp. 5980-5988; Spanget-Lansen, J., and Gleiter, R., Tetrahedron, 1983, vol. 39, no. 20, pp. 3345-3350; Carrupt, P.-A. and Vogel, P., J. Mol. Struct. (Theochem.), 1985, vol. 124, nos. 1-2, pp. 9-23; Rondan, N.G., Paddon, Row, M.N., and Carammella, P., Mareda, J., Mueller, P.H., and Houk, K.N., J. Am. Chem. Soc., 1982, vol. 104, no. 18, pp. 4974-4976.
14. 3. Freeman, F., Chem. Rev., 1975, vol. 75, no. 4, pp. 439-490; Kas'yan, L.I., Ctepanova, N.V., Bykov, M.V., and Malinovskii, M.C., Ukr. Khim. Zh., 1984, vol. 50, no. 6, pp. 633-637; Huisgen, R., Ooms, P.H.J., Mingin, M., and Allinger, N.L., J. Am. Chem. Soc., 1980, vol. 102, no. 11, pp. 3951-3953; Kas'yan, L.I., Gorb, L.G., Ctepanova, N.V., and Zefirov, N.C., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 893-897; Burkert, N., Angew. Chem., 1981, vol. 93, no. 6-7, pp. 602-603; Houk, K.N., Rondan, N.G. Brown, F.K., Jorgensen, W.L., Madura, J.D., and Spellmeyer, D.C., J. Am. Chem. Soc., 1983, vol. 105, no. 19, pp. 5980-5988; Spanget-Lansen, J., and Gleiter, R., Tetrahedron, 1983, vol. 39, no. 20, pp. 3345-3350; Carrupt, P.-A. and Vogel, P., J. Mol. Struct. (Theochem.), 1985, vol. 124, nos. 1-2, pp. 9-23; Rondan, N.G., Paddon, Row, M.N., and Carammella, P., Mareda, J., Mueller, P.H., and Houk, K.N., J. Am. Chem. Soc., 1982, vol. 104, no. 18, pp. 4974-4976.
15. 3. Freeman, F., Chem. Rev., 1975, vol. 75, no. 4, pp. 439-490; Kas'yan, L.I., Ctepanova, N.V., Bykov, M.V., and Malinovskii, M.C., Ukr. Khim. Zh., 1984, vol. 50, no. 6, pp. 633-637; Huisgen, R., Ooms, P.H.J., Mingin, M., and Allinger, N.L., J. Am. Chem. Soc., 1980, vol. 102, no. 11, pp. 3951-3953; Kas'yan, L.I., Gorb, L.G., Ctepanova, N.V., and Zefirov, N.C., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 893-897; Burkert, N., Angew. Chem., 1981, vol. 93, no. 6-7, pp. 602-603; Houk, K.N., Rondan, N.G. Brown, F.K., Jorgensen, W.L., Madura, J.D., and Spellmeyer, D.C., J. Am. Chem. Soc., 1983, vol. 105, no. 19, pp. 5980-5988; Spanget-Lansen, J., and Gleiter, R., Tetrahedron, 1983, vol. 39, no. 20, pp. 3345-3350; Carrupt, P.-A. and Vogel, P., J. Mol. Struct. (Theochem.), 1985, vol. 124, nos. 1-2, pp. 9-23; Rondan, N.G., Paddon, Row, M.N., and Carammella, P., Mareda, J., Mueller, P.H., and Houk, K.N., J. Am. Chem. Soc., 1982, vol. 104, no. 18, pp. 4974-4976.
16. 3. Freeman, F., Chem. Rev., 1975, vol. 75, no. 4, pp. 439-490; Kas'yan, L.I., Ctepanova, N.V., Bykov, M.V., and Malinovskii, M.C., Ukr. Khim. Zh., 1984, vol. 50, no. 6, pp. 633-637; Huisgen, R., Ooms, P.H.J., Mingin, M., and Allinger, N.L., J. Am. Chem. Soc., 1980, vol. 102, no. 11, pp. 3951-3953; Kas'yan, L.I., Gorb, L.G., Ctepanova, N.V., and Zefirov, N.C., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 893-897; Burkert, N., Angew. Chem., 1981, vol. 93, no. 6-7, pp. 602-603; Houk, K.N., Rondan, N.G. Brown, F.K., Jorgensen, W.L., Madura, J.D., and Spellmeyer, D.C., J. Am. Chem. Soc., 1983, vol. 105, no. 19, pp. 5980-5988; Spanget-Lansen, J., and Gleiter, R., Tetrahedron, 1983, vol. 39, no. 20, pp. 3345-3350; Carrupt, P.-A. and Vogel, P., J. Mol. Struct. (Theochem.), 1985, vol. 124, nos. 1-2, pp. 9-23; Rondan, N.G., Paddon, Row, M.N., and Carammella, P., Mareda, J., Mueller, P.H., and Houk, K.N., J. Am. Chem. Soc., 1982, vol. 104, no. 18, pp. 4974-4976.
17. 3. Freeman, F., Chem. Rev., 1975, vol. 75, no. 4, pp. 439-490; Kas'yan, L.I., Ctepanova, N.V., Bykov, M.V., and Malinovskii, M.C., Ukr. Khim. Zh., 1984, vol. 50, no. 6, pp. 633-637; Huisgen, R., Ooms, P.H.J., Mingin, M., and Allinger, N.L., J. Am. Chem. Soc., 1980, vol. 102, no. 11, pp. 3951-3953; Kas'yan, L.I., Gorb, L.G., Ctepanova, N.V., and Zefirov, N.C., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 893-897; Burkert, N., Angew. Chem., 1981, vol. 93, no. 6-7, pp. 602-603; Houk, K.N., Rondan, N.G. Brown, F.K., Jorgensen, W.L., Madura, J.D., and Spellmeyer, D.C., J. Am. Chem. Soc., 1983, vol. 105, no. 19, pp. 5980-5988; Spanget-Lansen, J., and Gleiter, R., Tetrahedron, 1983, vol. 39, no. 20, pp. 3345-3350; Carrupt, P.-A. and Vogel, P., J. Mol. Struct. (Theochem.), 1985, vol. 124, nos. 1-2, pp. 9-23; Rondan, N.G., Paddon, Row, M.N., and Carammella, P., Mareda, J., Mueller, P.H., and Houk, K.N., J. Am. Chem. Soc., 1982, vol. 104, no. 18, pp. 4974-4976.
18. 3. Freeman, F., Chem. Rev., 1975, vol. 75, no. 4, pp. 439-490; Kas'yan, L.I., Ctepanova, N.V., Bykov, M.V., and Malinovskii, M.C., Ukr. Khim. Zh., 1984, vol. 50, no. 6, pp. 633-637; Huisgen, R., Ooms, P.H.J., Mingin, M., and Allinger, N.L., J. Am. Chem. Soc., 1980, vol. 102, no. 11, pp. 3951-3953; Kas'yan, L.I., Gorb, L.G., Ctepanova, N.V., and Zefirov, N.C., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 893-897; Burkert, N., Angew. Chem., 1981, vol. 93, no. 6-7, pp. 602-603; Houk, K.N., Rondan, N.G. Brown, F.K., Jorgensen, W.L., Madura, J.D., and Spellmeyer, D.C., J. Am. Chem. Soc., 1983, vol. 105, no. 19, pp. 5980-5988; Spanget-Lansen, J., and Gleiter, R., Tetrahedron, 1983, vol. 39, no. 20, pp. 3345-3350; Carrupt, P.-A. and Vogel, P., J. Mol. Struct. (Theochem.), 1985, vol. 124, nos. 1-2, pp. 9-23; Rondan, N.G., Paddon, Row, M.N., and Carammella, P., Mareda, J., Mueller, P.H., and Houk, K.N., J. Am. Chem. Soc., 1982, vol. 104, no. 18, pp. 4974-4976.
19. 4. Kas'yan, L.I., Usp. Khim., 1998, vol. 67, no. 4, pp. 299-316; Kas'yan, L.I., Seferova, M.F. and Okovityi, C.I., Alitsiklicheskie epoksidnye soedineniya. Metody sinteza (Alicyclic Epoxyde Compounds. Synthesys Methods), Dnepropetrovsk: Izd. DGU, 1996, 191 p.; Klumpp, C.W., Veefkind, A.H., de Graaf, W.L., and Bichelhaupt, T., Lieb. Ann., 1967, vol. 706, no. 1, pp. 47-67; Brown, H.C., Kawakami, J.H., and Ikegami, S., J. Am. Chem. Soc., 1970, vol. 92, no. 23, pp. 6914-6917; Zefirov, N.S., Kasyan, L.I., Gnedenkov, L.Yu., Shashkov, A.S., and Cherepanova, E.G., Tetrahedron Lett., 1979, no. 11, pp. 949-950; Paddon-Row, M.N., Patney, H.K., and Warrener, R.N., J. Org. Chem., 1979, vol. 44, no. 22, pp. 3908-3917; Lazurin, E.A., Voronenkov, V.V., and Osokin, Yu.G., Usp. Khim., 1977, vol. 46, no. 10, pp. 1737-1756.
20. 4. Kas'yan, L.I., Usp. Khim., 1998, vol. 67, no. 4, pp. 299-316; Kas'yan, L.I., Seferova, M.F. and Okovityi, C.I., Alitsiklicheskie epoksidnye soedineniya. Metody sinteza (Alicyclic Epoxyde Compounds. Synthesys Methods), Dnepropetrovsk: Izd. DGU, 1996, 191 p.; Klumpp, C.W., Veefkind, A.H., de Graaf, W.L., and Bichelhaupt, T., Lieb. Ann., 1967, vol. 706, no. 1, pp. 47-67; Brown, H.C., Kawakami, J.H., and Ikegami, S., J. Am. Chem. Soc., 1970, vol. 92, no. 23, pp. 6914-6917; Zefirov, N.S., Kasyan, L.I., Gnedenkov, L.Yu., Shashkov, A.S., and Cherepanova, E.G., Tetrahedron Lett., 1979, no. 11, pp. 949-950; Paddon-Row, M.N., Patney, H.K., and Warrener, R.N., J. Org. Chem., 1979, vol. 44, no. 22, pp. 3908-3917; Lazurin, E.A., Voronenkov, V.V., and Osokin, Yu.G., Usp. Khim., 1977, vol. 46, no. 10, pp. 1737-1756.
21. 4. Kas'yan, L.I., Usp. Khim., 1998, vol. 67, no. 4, pp. 299-316; Kas'yan, L.I., Seferova, M.F. and Okovityi, C.I., Alitsiklicheskie epoksidnye soedineniya. Metody sinteza (Alicyclic Epoxyde Compounds. Synthesys Methods), Dnepropetrovsk: Izd. DGU, 1996, 191 p.; Klumpp, C.W., Veefkind, A.H., de Graaf, W.L., and Bichelhaupt, T., Lieb. Ann., 1967, vol. 706, no. 1, pp. 47-67; Brown, H.C., Kawakami, J.H., and Ikegami, S., J. Am. Chem. Soc., 1970, vol. 92, no. 23, pp. 6914-6917; Zefirov, N.S., Kasyan, L.I., Gnedenkov, L.Yu., Shashkov, A.S., and Cherepanova, E.G., Tetrahedron Lett., 1979, no. 11, pp. 949-950; Paddon-Row, M.N., Patney, H.K., and Warrener, R.N., J. Org. Chem., 1979, vol. 44, no. 22, pp. 3908-3917; Lazurin, E.A., Voronenkov, V.V., and Osokin, Yu.G., Usp. Khim., 1977, vol. 46, no. 10, pp. 1737-1756.
22. 4. Kas'yan, L.I., Usp. Khim., 1998, vol. 67, no. 4, pp. 299-316; Kas'yan, L.I., Seferova, M.F. and Okovityi, C.I., Alitsiklicheskie epoksidnye soedineniya. Metody sinteza (Alicyclic Epoxyde Compounds. Synthesys Methods), Dnepropetrovsk: Izd. DGU, 1996, 191 p.; Klumpp, C.W., Veefkind, A.H., de Graaf, W.L., and Bichelhaupt, T., Lieb. Ann., 1967, vol. 706, no. 1, pp. 47-67; Brown, H.C., Kawakami, J.H., and Ikegami, S., J. Am. Chem. Soc., 1970, vol. 92, no. 23, pp. 6914-6917; Zefirov, N.S., Kasyan, L.I., Gnedenkov, L.Yu., Shashkov, A.S., and Cherepanova, E.G., Tetrahedron Lett., 1979, no. 11, pp. 949-950; Paddon-Row, M.N., Patney, H.K., and Warrener, R.N., J. Org. Chem., 1979, vol. 44, no. 22, pp. 3908-3917; Lazurin, E.A., Voronenkov, V.V., and Osokin, Yu.G., Usp. Khim., 1977, vol. 46, no. 10, pp. 1737-1756.
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